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Stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer

Shi, Qixun LU ; Javorskis, Tomas; Bergquist, Karl Erik LU ; Ulčinas, Arturas; Niaura, Gediminas; Matulaitien, Ieva; Orentas, Edvinas and Wärnmark, Kenneth LU (2017) In Nature Communications 8.
Abstract

The design and synthesis of new stimuli-responsive hydrogen-bonding monomers that display a diversity of self-assembly pathways is of central importance in supramolecular chemistry. Here we describe the aggregation properties of a simple, intrinsically C2-symmetric enantiopure bicyclic cavity compound bearing a terminally unsubstituted ureidopyrimidinone fragment fused with a pyrrole moiety in different solvents and in the absence and presence of C60 and C70 guests. The tetrameric cyclic aggregate is selectively obtained in chlorinated solvents, where only part of the available hydrogen bonding sites are utilized, whereas in toluene or upon addition of C70 guests, further aggregation into... (More)

The design and synthesis of new stimuli-responsive hydrogen-bonding monomers that display a diversity of self-assembly pathways is of central importance in supramolecular chemistry. Here we describe the aggregation properties of a simple, intrinsically C2-symmetric enantiopure bicyclic cavity compound bearing a terminally unsubstituted ureidopyrimidinone fragment fused with a pyrrole moiety in different solvents and in the absence and presence of C60 and C70 guests. The tetrameric cyclic aggregate is selectively obtained in chlorinated solvents, where only part of the available hydrogen bonding sites are utilized, whereas in toluene or upon addition of C70 guests, further aggregation into tubular supramolecular polymers is achieved. The open-end cyclic assemblies rearrange into a closed-shell capsule upon introduction of C60 with an accompanied symmetry breaking of the monomer. Our study demonstrates that a C60 switch can be used to simultaneously control the topology and occupancy of tubular assemblies resulting from the aggregation of small monomers.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Nature Communications
volume
8
publisher
Nature Publishing Group
external identifiers
  • scopus:85017439384
  • wos:000399082000001
ISSN
2041-1723
DOI
10.1038/ncomms14943
language
English
LU publication?
yes
id
f8468304-9fb0-4b67-887a-7b4b16be4c9b
date added to LUP
2017-05-08 12:17:12
date last changed
2017-09-18 11:35:21
@article{f8468304-9fb0-4b67-887a-7b4b16be4c9b,
  abstract     = {<p>The design and synthesis of new stimuli-responsive hydrogen-bonding monomers that display a diversity of self-assembly pathways is of central importance in supramolecular chemistry. Here we describe the aggregation properties of a simple, intrinsically C<sub>2</sub>-symmetric enantiopure bicyclic cavity compound bearing a terminally unsubstituted ureidopyrimidinone fragment fused with a pyrrole moiety in different solvents and in the absence and presence of C<sub>60</sub> and C<sub>70</sub> guests. The tetrameric cyclic aggregate is selectively obtained in chlorinated solvents, where only part of the available hydrogen bonding sites are utilized, whereas in toluene or upon addition of C<sub>70</sub> guests, further aggregation into tubular supramolecular polymers is achieved. The open-end cyclic assemblies rearrange into a closed-shell capsule upon introduction of C<sub>60</sub> with an accompanied symmetry breaking of the monomer. Our study demonstrates that a C<sub>60</sub> switch can be used to simultaneously control the topology and occupancy of tubular assemblies resulting from the aggregation of small monomers.</p>},
  articleno    = {14943},
  author       = {Shi, Qixun and Javorskis, Tomas and Bergquist, Karl Erik and Ulčinas, Arturas and Niaura, Gediminas and Matulaitien, Ieva and Orentas, Edvinas and Wärnmark, Kenneth},
  issn         = {2041-1723},
  language     = {eng},
  month        = {04},
  publisher    = {Nature Publishing Group},
  series       = {Nature Communications},
  title        = {Stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer},
  url          = {http://dx.doi.org/10.1038/ncomms14943},
  volume       = {8},
  year         = {2017},
}